ID: ALA377324

Max Phase: Preclinical

Molecular Formula: C32H22O10

Molecular Weight: 566.52

Molecule Type: Small molecule

Representations

Synonyms (1): Ginkgetin
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(O)c2c(=O)cc(-c3ccc(OC)c(-c4c(O)cc(O)c5c(=O)cc(-c6ccc(O)cc6)oc45)c3)oc2c1

Standard InChI:  InChI=1S/C32H22O10/c1-39-18-10-20(34)30-23(37)13-27(41-28(30)11-18)16-5-8-25(40-2)19(9-16)29-21(35)12-22(36)31-24(38)14-26(42-32(29)31)15-3-6-17(33)7-4-15/h3-14,33-36H,1-2H3

Standard InChI Key:  AIFCFBUSLAEIBR-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 566.52

Molecular Weight (Monoisotopic): 566.1213

AlogP: 5.74

#Rotatable Bonds: 5

Polar Surface Area: 159.80

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.23

CX Basic pKa:

CX LogP: 5.38

CX LogD: 3.85

Aromatic Rings: 6

Heavy Atoms: 42

QED Weighted: 0.20

Np Likeness Score: 1.02

References

1. Lee MK, Lim SW, Yang H, Sung SH, Lee HS, Park MJ, Kim YC..  (2006)  Osteoblast differentiation stimulating activity of biflavonoids from Cephalotaxus koreana.,  16  (11): [PMID:16574412] [10.1016/j.bmcl.2006.03.018]

2. Miki K, Nagai T, Suzuki K, Tsujimura R, Koyama K, Kinoshita K, Furuhata K, Yamada H, Takahashi K..  (2007)  Anti-influenza virus activity of biflavonoids.,  17  (3): [PMID:17110111] [10.1016/j.bmcl.2006.10.075]

3. Pattamadilok D, Suttisri R..  (2008)  Seco-terpenoids and other constituents from Elateriospermum tapos.,  71  (2): [PMID:18179177] [10.1021/np070629g]

4. Sun CM, Syu WJ, Huang YT, Chen CC, Ou JC..  (1997)  Selective cytotoxicity of ginkgetin from Selaginella moellendorffii.,  60  (4): [PMID:9134745] [10.1021/np960608e]

5. Mercader AG, Pomilio AB..  (2010)  QSAR study of flavonoids and biflavonoids as influenza H1N1 virus neuraminidase inhibitors.,  45  (5): [PMID:20116898] [10.1016/j.ejmech.2010.01.005]

6. Sasaki H, Miki K, Kinoshita K, Koyama K, Juliawaty LD, Achmad SA, Hakim EH, Kaneda M, Takahashi K..  (2010)  beta-Secretase (BACE-1) inhibitory effect of biflavonoids.,  20  (15): [PMID:20598535] [10.1016/j.bmcl.2010.06.021]

7. Ryu YB, Jeong HJ, Kim JH, Kim YM, Park JY, Kim D, Nguyen TT, Park SJ, Chang JS, Park KH, Rho MC, Lee WS..  (2010)  Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL(pro) inhibition.,  18  (22): [PMID:20934345] [10.1016/j.bmc.2010.09.035]

8. Wong IL, Chan KF, Chan TH, Chow LM..  (2012)  Flavonoid dimers as novel, potent antileishmanial agents.,  55  (20): [PMID:22989363] [10.1021/jm301172v]

9. You OH, Kim SH, Kim B, Sohn EJ, Lee HJ, Shim BS, Yun M, Kwon BM, Kim SH..  (2013)  Ginkgetin induces apoptosis via activation of caspase and inhibition of survival genes in PC-3 prostate cancer cells.,  23  (9): [PMID:23523142] [10.1016/j.bmcl.2013.02.080]

10. Sasaki H, Kitoh Y, Tsukada M, Miki K, Koyama K, Juliawaty LD, Hakim EH, Takahashi K, Kinoshita K..  (2015)  Inhibitory activities of biflavonoids against amyloid-β peptide 42 cytotoxicity in PC-12 cells.,  25  (14): [PMID:26004578] [10.1016/j.bmcl.2015.04.106]

11. Sirimangkalakitti N, Juliawaty LD, Hakim EH, Waliana I, Saito N, Koyama K, Kinoshita K..  (2019)  Naturally occurring biflavonoids with amyloid β aggregation inhibitory activity for development of anti-Alzheimer agents.,  29  (15): [PMID:31138471] [10.1016/j.bmcl.2019.05.020]

12. Lin L, Lu L, Yuan C, Wang A, Zhu M, Fu X, Xing S..  (2021)  The dual inhibition against the activity and expression of tyrosine phosphatase PRL-3 from a rhodanine derivative.,  41  [PMID:33766767] [10.1016/j.bmcl.2021.127981]

13. Zhang S, Sun Y, Yao F, Li H, Yang Y, Li X, Bai Z, Hu Y, Wang P, Xu X..  (2023)  Ginkgo Biflavones Cause p53 Wild-Type Dependent Cell Death in a Transcription-Independent Manner of p53.,  86  (2.0): [PMID:36700552] [10.1021/acs.jnatprod.2c00959]

Source

Source(1):

• Scientific Literature